Based mainly on HMR evidence of the crude ether wash, DOPAL can be made and isolated in 5-10% yield as a major product after a brief (15 min) decomposition of adrenaline in 85% phosphoric acid at 100-120 C. This material is not quite pure enough to be used without chromatography.
Ugi Reaction
The imine was not reversed to the aldehyde and no crystalline Ugi product was formed however some of the Ugi product was formed compared to previous NMR were the Ugi product was isolated.
Imine Reversal
Boc-Gly-OH alone is sufficient to reverse partial imine formation between piperonal and t-butyl amine in methanol. Experiments to remove the water from the imine reaction and then add the acid should be preformed to see if the imine reversal by Boc-Gly-OH can be blocked.
Conclusions
DOPAL
Based mainly on HMR evidence of the crude ether wash, DOPAL can be made and isolated in 5-10% yield as a major product after a brief (15 min) decomposition of adrenaline in 85% phosphoric acid at 100-120 C. This material is not quite pure enough to be used without chromatography.Ugi Reaction
The imine was not reversed to the aldehyde and no crystalline Ugi product was formed however some of the Ugi product was formed compared to previous NMR were the Ugi product was isolated.Imine Reversal
Boc-Gly-OH alone is sufficient to reverse partial imine formation between piperonal and t-butyl amine in methanol. Experiments to remove the water from the imine reaction and then add the acid should be preformed to see if the imine reversal by Boc-Gly-OH can be blocked.Back to my page
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